Wilson played for the Saskatoon, Saskatchewan, Mayfair Public School hockey team. In 1937, Mayfair won the J.D. McDonald Cup for Saskatoon public schools Hockey Championship, with Ken playing center and left wing.

For three seasons, starting in 1960, Ken was the General Manager of the Omaha Knights in the IHL.

In 1963, Wilson moved to Toledo, Ohio, where he owned and started the Toledo Blades in the IHL. Over the next three seasons, he filled the roll of General Manager and as a mid season replacement in 1966, coach. In 1964, the Toledo Blades won the Fred A. Huber Trophy, awarded for "Most Points in the Regular Season' and the Turner Cup awarded to the Playoff Champions.

In 1967 the National Hockey League expanded and Bert Olmstead was hired as General Manager and Coach of Oakland Seals after the June 7, 1967 NHL player draft. Olmstead hired Wilson, with the plan of Wilson running a farm team the following season. The entire hockey staff was fired at the end of the first season.

Wilson was assistant manager of the Muskegon Mohawks in the IHL for two seasons, 1970-1971 and 1971-1972.

In 1972 Wilson was hired as General Manager of the Des Moines, Iowa franchise in the IHL. Feeling the franchise needed a new look and image, Wilson, changed the name to the Des Moines Capitols. In 1973-1974, the Capitols won the Fred A. Huber Trophy and the Turner Cup. This was the only season the a Des Moines based IHL team finished first and won the playoffs. The Capitols disbanded in 1975.

In 1981, Wilson formed a group of investors to put an IHL team in Peoria, Illinois. The Peoria Prancers, began play, with the 1982-1983 season. After years of good labor relations, the United Auto Workers went on strike against Caterpillar Inc. on October 1, 1982. At the time 50% of Peorians were employed directly or indirectly by Caterpillar. The strike lasted the entire first hockey season. The Prancers were never able to recover from the effects of the strike and folded after the 1983-1984 season.